Rebel Without a Crew: A Lyft Story – Prologue
How a Hollywood dropout found his ride through the early days of a unicorn startup.
Prologue
I’ve carried my story from Lyft with me for years: scribbled notes, half-finished journal entries, photos, vivid memories of a wild ride through the early days of a unicorn startup. Lately, I’ve felt the urge to piece it all together and share it – not just out of nostalgia, but to remember what it was like to build something from nothing.
Let’s start at the end…
October 30, 2014
The building at the corner of 19th and Harrison was Lyft’s stronghold at the peak of the Rideshare Wars. A 67,000-square-foot, three-story fortress nestled in the Mission district. Sure, it paled in comparison to the Death Star building that Travis Kalanick’s Uber called home over at 1455 Market, but it was a fitting headquarters for the alternative to Uber – the "friend with a car" brand that Lyft embraced.
I will always love the Mission. It was my home for 5 years before moving in with my now wife and relocating to Lower Nob Hill. Lyft HQ was a short walk, and an even shorter Lyft ride, from my apartment at 16th and Dolores.
I got to the office around 8 a.m. that day, later than usual. A few people were milling about – the ones who worked all night and clearly never went home (startup life), and the well-rested cool kids trickling in from morning yoga or spin class. I hadn’t started my yoga journey at this point, though I probably should have.
I wore J. Crew button-downs like they were going out of style, paired with Levi's jeans and New Balance shoes. If it got cold, I’d throw on one of my many Lyft hoodies. I now had spending cash, so I upgraded my wardrobe. For me it was stylish yet comfortable, just the way I like it.
At this point, the company had 400+ employees – a mind-blowing number considering a year earlier we had just cracked 100. We had cycled through several HQs in the past 18 months, outgrowing each space like a weed. Every week, I saw more new faces walking around the office with shiny MacBooks, fresh swag (likely sourced by my team), and eager smiles.
I didn’t know most of them, but they usually knew me. Or at least knew of me.
An interaction would go something like:
"You’re the shipping guy, right? I’ve heard all about you."
When I was hired, my official title was Shipping Lead, but I quickly changed it the day everyone was issued business cards. (More on that in a later chapter.)
Honestly, I never liked being known as the "shipping guy." I felt like it oversimplified my contributions to Lyft’s growth. My role wasn’t just shipping – it was company-building and running a logistics operation.
I probably spent too much time at the office. I ate breakfast and lunch there daily, sometimes dinner, and often worked Saturdays. Sundays were my day off, but I was always thinking about the upcoming week. Great for my grocery budget, not so great for my social life.
Fake startup influencer types will tell you it’s 24/7/365 or some bullshit – and while it can be, it’s not sustainable. Especially if you’re busy chasing engagement by writing trite social media posts full of self-aggrandizing platitudes.
I was burnt out. I needed a vacation.
During my time at Lyft, I had taken just one day off, to attend my dad’s funeral back in Stockton. I remember taking my work laptop in my backpack and periodically checking in during the family gathering. I wasn’t super close with my dad but his death still impacted me, and in retrospect, I should have left the laptop behind and taken time to decompress.
I should’ve booked that Virgin Atlantic flight to London.
That morning, my fuel was pour-over coffee with creamer and sugar, paired with toast and avocado, a hard-boiled egg or two, and a banana. Kudos to Corey Lambert, the best office experience manager in tech.
One of the many skills I picked up at Lyft was the art of the pour-over, thanks to Colin Frolich. A former Starbucks marketing guy, Colin taught a few of us the craft. It became a nice little ritual where I could focus on the details of my morning nectar – very zen, very tasty. These days, Colin is the founder and CEO of Placemate.
I got to my desk and flipped open my laptop. I had been working with a potential new partner to reduce the cost of our newest onboarding kit. For context, anyone who wanted to be a Lyft driver had to complete a background check and identity verification. Once approved, they were shipped a driver kit: a pink carstache, Lyft stickers, FAQs, and other essentials. These kits were fun to build.
I had sent samples to a startup run by two young guys who had likely realized we were shipping truckloads of these kits weekly. They claimed to have better pricing. Okay, bring it on!
By then, I was getting more cold calls from companies wanting to partner with Lyft in some way: as a supplier, a 3PL, or a tech solution. We were a huge deal now. Gone were the days when I got laughed at and hung up on.
I’m the captain now, bitch.
Their proposal projected savings in the neighborhood of $3 million annually. Some weeks, we were shipping 2,000-3,000 kits. Crazy to think that a year earlier, I was assembling these kits by myself in a back room at the old Oakland office.
I sat back and reflected on my journey on the Drive Team, what we early employees called the OG Ops team. We grew up together and helped take the company from obscurity to national attention. Jerry Seinfeld was once photographed wearing a pink mustache for a magazine shoot.
Even my mom was like, “I saw your company on TV.”
Hyper-growth is no joke, folks.
I glanced up at a small sign on the back of Matt "Disko" Earnest’s monitor.
It read: "I’d take a Nerf bullet for you."
Disko was one of the original San Francisco Lyft drivers, a legend in the community, back when they decorated their cars to reflect their personalities. His car was a full-blown DJ setup: intelligent lighting, a karaoke machine, and turntables. The phrase on his monitor embodied the cheeky attitude many of us early Lyft employees adopted during the Wartime era of Rideshare. The days were long. The work was intense. It was fun, but also brutal. Yet we always had each other’s backs. These days Matt is a Handyman and Council Member in the town of Mountain House, just outside of Tracy, CA.
Then came the message that would change everything.
A ping from my manager, also named Matt: “Hey, do you have a moment to meet downstairs in such-and-such conference room?”
I furrowed my brow and took another sip of coffee. I glanced at my coordinator, Karynn, but didn’t say anything. Too early for bad news, I thought.
Matt had been assigned to me after the abrupt departures of my original bosses, Steve Schnell and Travis VanderZanden. Someone said Matt was a rockstar. Apparently, he tightened up operations at a previous company.
Steve and Travis would eventually land at rival Uber.
I made my way downstairs past a wall of employee photos: group shots, candids, memories. A warm touch to HQ.
I walked into the conference room, laptop under my arm. Kelsey from People Ops was already there. Her face was unreadable.
Remember that scene from Goodfellas when Joe Pesci’s character Tommy DeVito gets whacked? Felt kinda like that, except one of the walls was covered in pink fur.
I took a seat.
Matt sat in front of the pink fur wall. It felt like an episode of Silicon Valley.
"We no longer have a place for you on the team. Today is your last day," he started.
Record scratch.
"Can you give me 24 hours to find another team? I’ve seen others that were given that opportunity when teams and roles were eliminated." I fired back.
"We asked. No one wants you," Matt shot back.
No one wants you.
Oof.
Matt mumbled something about performance, but the only example he gave was a delayed email reply from weeks ago. It was also the first time anyone had raised a concern about my performance.
“There’s no longer a place for you on this team. Sorry.” He finished.
Truth is, I should’ve seen it coming. When the new VP of Ops, Woody, dismissed all of my work and told me that I’d have to start from scratch under his regime, it was a sign. People were getting pushed out. I wasn’t the only one.
Kelsey slid the separation docs across the table on cue. I examined them.
"Can I get a moment alone, please?" I asked.
Alone in that cold conference room, I accepted my fate. The company I helped build no longer wanted me. Lyft had given me a chance to go from zero to one, professionally and personally.
The ink on John Zimmer’s signature looked so fresh.
I had been unceremoniously dumped by one of the hottest startups in tech.
I was sad, but also relieved.
Let’s go back to the beginning.
FADE TO BLACK
🎧 Cue “Let’s Stay Together” – Al Green.
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Next stop: Chapter 1 – Hollywood, Hondas, and Carstaches
Damn, I thought it started at Chapter 1! NOOOOOOO…